Cottage holiday rentals in Bailey Island

A great spot tucked away!! House was cute and as shown in the pictures, is right on the water and has some great views! It rained the majority of the time we were there so didn’t get to take advantage of all the outdoor amenities, but would have if better weather! Host was very friendly, communicative and responsive!

We had a great two nights here and enjoyed the hot soak and the sauna. It was near many amenities and also felt very removed. Matt’s was attentive without being intrusive, making sure our stay was perfect and the escape we hoped it would be.

Adorable cottage, newly renovated. Perfect for two with an open space loft for one more. Kitchen is well stocked right down to the coffee. A good location if visiting Fort Knox, Mt. Barrie and not too far from Bar Harbor if that is on your list. Great stay, highly recommend. Beautiful view and private.

Great clean air bnb. Accurately as described.. looks good in photos but even better in-person. Bed was comfortable. Would rent their properties again.

Perfect for what we needed for a weekend getaway. So peaceful and a lot of interesting wildlife. We saw so many different types of birds! The hot tub is spacious and easy to use.

We’ve stayed in a lot of Airbnbs across the country and I’m not exaggerating when I say that Lydia’s place was one of the cleanest and most well-maintained homes that we’ve been in. The property and scenery are breathtaking. The numbers of birds and chipmunks that entertained us while we sat on the back deck was surprising. We ate all of our meals with the exception of lunches at the cabin and had everything we needed to prep and cook our food. This trip was all about relaxing and Lydia’s home was everything we needed.

We had a wonderful stay here and highly recommend it! The location is great, as it’s close to plenty of restaurants and stores. We were even able to walk to get breakfast and dinner. The space itself was much larger than we expected and very clean. The kitchen had everything we needed and we even had snacks, waters, and coffee left for us! The highlight for my 2 year old was the pirate ship playground. We also loved having access to picnic tables. We got takeout and enjoyed eating outdoors. We did not use the outside grill but that is a great addition and we would have used if we stayed longer. The host was very helpful and accommodating. They offered early check in and check out and gave very clear instructions on how to get in. I would not hesitate to return in the future!

The cottage is spotless, well-stocked and conveniently located for day trips in any direction. This is our 4th year staying at this lovely cottage for a pre-holidays getaway. We look forward to keeping this annual tradition!

We had a fantastic time at this cute and cozy cottage! It’s within 15 minutes of basically anything in the Portland area and the cottage itself is so charming and inviting. We only wish we had planned to stay here longer!

Tammy describes her sweet cottage perfectly. Water views are spectacular with options to fish off the dock, sit in the backyard to warm up or sit on the bluff to cool off. It was perfect for this girl and her dog to re-set in solitude. Most places on the water have sensitive septic as described so you want to consider that if there are more than two guests. I enjoyed my endless walks on Popham beach (no dogs 4/1-10/1)) and was thrilled to be there in the off season. I barely saw anyone! Reid State Park was also spectacular and more opportunity to walk my dog on the trails. Tick season is a bit of an adjustment every year but not a problem if you prepare yourself and your furry friends. A perfect place for a great book, wandering around historic Bath, and easy meal prep. I stayed 2 weeks and appreciated all the thought Tammy put into anticipating what a traveler might need.

Our stay at Jeff’s cottage was one of the most relaxing since we began our yearly mother-daughter long weekend getaway tradition about 8 years ago. The cottage is rustic, yet cute, comfortable, and clean and the setting is simply beautiful. Some highlights were foggy harbor explorations by kayak, sunset happy hours at the harbor shore, and napping to the sound of the rain on the metal roof. The minimal steps and level front yard made it possible for our mother to enjoy the setting and access the harbor with us. We especially appreciated a freezer full of ice upon our arrival :) We hope to return next June. Highly recommend!

Barbara place is awesome for a couple plus I child nice quiet area very clean and it private. Barbara is a great host you will love this spot it feels like home we will be back

We had such a great time staying at Emily's awesome retreat. It was our first mini-vacation with our dog and we were looking for some peaceful, wide open space to let her roam free. We absolutely got that with this home and thoroughly enjoyed the town, as well. Emily was super responsive whenever we did have a question and provided us with a great list of places to check out around town. Would absolutely stay again. Thanks!

We loved staying at Ann's place! It was exactly what we wanted, close to town and to lots of activities but also felt remote and in a really gorgeous location. Great, rustic spot.

Perfect little Maine cabin getaway! We enjoyed our stay so much. The cabin was clean, easy to find, and had everything we needed for four people and two dogs. Cannot recommend enough!

Enjoyed staying at this cottage at Sheepscot Village. Very clean & responsive host. Look forward to staying again.

Great cottage right on the lake! Kayaks were great to take out and explore the lake and see wildlife as well. The cottage is spacious and comfortable. The kitchen is large and well appointed for any cooking you may want to do. Grill and plenty of beach chair/ towels available as well. Adam is extremely responsive and I highly recommend. The place is quite peaceful though the lake gets pretty busy on the weekends with boats but not in an obnoxious way. Loved sipping coffee and reading on the dock each morning. Will definitely book again!

A very cozy, charming cottage right on the ocean! Beautiful! Would definitely recommend to all that want a secluded, private area to stay in!

Dan and Jane have a beautiful home. They were extremely kind and I can’t thank them enough for allowing me and the kids to meet their horses. It is a wonderful property on a serene landscape. The pictures don’t do it justice. We will certainly be back.

My wife and I stayed at Viktor's place for our honeymoon. As soon as we walked through the door it felt like we were in a second home. We loved using the projector and home theater setup to play Nintendo Switch and watch Netflix. I liked that the bedroom had its own separate A/C unit from the living room. Made it so much easier to set the temperature during the day and evening. The combined washer/dryer unit worked great and didn't have any issues drying our clothes. Nearly every morning we were greeted by neighboring deer who came to feed on the backyard grass. The surrounding area (Georgetown, Bath, and Boothbay Harbor) are really great to find good food, parks, and entertainment nearby. I highly recommend this place. It really is a gem in the middle of the forest.

Being at Carole's place was a total pleasure. If I could, I'd spend a lot of time living on a boat, and this was about as close as possible to that experience, only much more comfortable. I loved being able to see all that was going on in the bay - a lobster boat with a happy dog aboard, a kayak - but mostly birds, including a few visits from a couple of Bald Eagles. For anyone who enjoys nature and privacy, this place is heaven.

We couldn’t be happier with our stay at Seaglass Cottage. From the moment we walked in, we were enchanted by the homey charm and solitude. As a grand finale, we were able to watch a northern lights show from the dock on our last night.

Steve and Desni's Lakefront home was spectacular! The lakefront views were stunning. The house was as described and provided everything we needed for a wonderful family vacation. Was very clean and tidy upon arrival. Room layouts provided ample space for our group of 10 (could have fit a couple more comfortably) and included all the amenities for indoor and outdoor fun! Zero complaints or cons for renting their home. Would highly recommend it.

The Eagles Nest is an amazing space! We stayed for 4 days and didn't want to leave. The view is beautiful and you must wake early to watch the sunrises. We even saw an eagle. Shannon was very responsive to all messages and super helpful when we needed to leave a different rental property (not one of hers). The home is immaculate. I can't say enough about The Eagles Nest and Shannon.